Find the top rated horseback riding trails in Pittsfield, whether you're looking for an easy short horseback riding trail or a long horseback riding trail, you'll find what you're looking for. Click on a horseback riding trail below to find trail descriptions, trail maps, photos, and reviews.
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We rode from Pittsfield to Adams and back. Very nice trail. 50% shaded. Ate lunch at AJ‘s at Adams. Nice restaurant in an old train depot. Limited parking at the beginning in Pittsfield. Start your ride at the next parking area to the north. Lots of lakes and rivers running next to the trail. Asphalt the entire length of the trail.
Decent walk and view. As of October 2026 bathrooms are not open ever.
We rode the whole trail. It's smooth, scenic, and frequently bathrooms. The leaves are turning, such a beautiful trail. A must ride. It should be a Hall of Fame trail.
We did this trail in two days. We learned that it is not quite complete from Hillsdale to Wassaic. Trail is closed from Black Grocery Road to Orphan Farm Road about 1.5 miles. So be warned that as of Sept 15 you can’t quite go completely through YET. Above Millerton and below are almost two completely different trails so we were happy to be able to stop and explore at our leisure. Above is really farm and marsh lands while below has more towns and historical things to see and do. Millerton, has many places to eat and a great mid stop. The leaves are not turning yet but will be beautiful in the colorful fall. I heartily recommend the ride.
Rode entire trail roundtrip on a sunny August day. It's a great trail with a great paved surface. Scenic, too. The southern trailhead (Wassaic) has a direct train connection to New York City, so it's just a matter of time before it's discovered by folks from the city for a day's ride.
Town of Millerton in center of trail had the best facilities for a mid-ride break. Copake Iron Works Museum at Taconic State Park and close to the trail also well worth a visit.
Biked end to end on a beautiful summer day. An absolutely beautiful paved trail with lots of water features to see - lakes to the south, river further north, and views of the mountains. Nice trailside pub in Adams and other eateries, including ice cream. Well-loved, with lots of walkers and skaters, as well as riders. Benches and picnic tables aplenty. One of the best trails I've had the privilege to ride. The only way it could possibly be better is if it was longer.
Correction to someone else's review: trail goes gently downhill south to north (not north to south) from Cheshire to Adams.
If you are a dedicated mountain biker than this would be a 5 star. Don't do this trail if you don't have a mountain bike or those fat tires. I was on a mountain bike, and my son had a regular bike. The beginning of the trail is easy and lovely. Once you connect with the trail (beautiful water views) the trail becomes mostly rock with some sand. Passed 1.8 miles the trail is impassable with our bikes. Somehow we made it out and back without falls or bike damage. I have biked other ski trails that were more compacted sand and dirt with some rock. This is not that kind of trail.
Loved this trail easy to ride. Well paved and clean. Will do this again and again.
Hubby & I went this morning for a trial run with my new e-bike! It was tons of fun!!!!
Awesome trail. Smooth surface and great views. Also lots of different places you can join the trail. We started a little further north to skip the more industrial part of the trail.
Beautiful 1st ride on the Norwottuck Rail Trail. We parked at the Marshalls in Hadley (trail starts right behind the building) and road a little over 10 miles into EastHampton and back. It was a very easy ride (my 1st ride of this length) on asphalt.
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